Copper catalysis with redox-active ligands

• Agnideep Das,
• Yufeng Ren,
• Cheriehan Hessin and
• Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

• alcohol to benzaldehyde, the authors also show that reaction with t-BuPhCuO.S.2 (5 mol %) could be efficiently extended to other substrates containing weak C–H bonds and acidic O–H bonds such as diphenylmethanol (PhBzOH), benzoin, and cinnamyl alcohol. However, alcohols with stronger C–H bonds

A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols

• Anna Czarnecka,
• Emilia Kowalska,
• Agnieszka Bodzioch,
• Joanna Skalik,
• Marek Koprowski,
• Krzysztof Owsianik and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2018, 14, 1229–1237, doi:10.3762/bjoc.14.105

• diphenylmethanol to diphenylmethane, described in literature [64], encouraged us to try the Pd-catalyzed reduction of the oxygen analog 9 (X = O) as a representative of the ortho-1,3-dioxanyl series. In this case, instead of the expected ortho-1,3-dioxanyl diarylmethane analog of 8b, 1,3-dihydroisobenzofuran 10

An alternative to hydrogenation processes. Electrocatalytic hydrogenation of benzophenone

• Cristina Mozo Mulero,
• Alfonso Sáez,
• Jesús Iniesta and
• Vicente Montiel

Beilstein J. Org. Chem. 2018, 14, 537–546, doi:10.3762/bjoc.14.40

• synthesis of diphenylmethanol upon the lowest current density. With regards to an increase by ten times the Pd electrocatalytic loading the electrocatalytic hydrogenation led neither to an increase in fractional conversion nor to a change in selectivity. Keywords: benzophenone; diphenylmethanol

• a more complex aromatic ketone dictated by the presence of two phenyl rings, in order to analyse fractional conversion and selectivity of formed products. Here, the main obtained product is diphenylmethanol (ketone conversion to alcohol) as a high added value product in chemical industry. Even

• hydrogenation at Pd0.02/C/T electrode. An inspection of the chromatograms confirms the formation of two final products corresponding to diphenylmethanol (Ph2CHOH) and diphenylmethane (Ph2CH2). Table 1 compiles fractional conversion of Ph2CO (XR), product yield of Ph2CHOH and Ph2CH2 (η), selectivity of Ph2CHOH

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

• , cyclizine, and buclizine derivatives [23]. These drugs belong to the antihistamine family. The process involves 4 reaction steps and two liquid–liquid extraction steps (for cinnarizine and buclizine derivatives). In the first step diphenylmethanol (1 equiv) is mixed with HCl (3 equiv) and passed through a

• process. Initially, the flow rate of diphenylmethanol and the alcohol derivative should be fixed at the desired set point using a control valve. These streams can be preheated using a heat exchanger with feedback control. Aqueous HCl can also be preheated to the reaction temperature by applying suitable

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

• Martin Obst and
• Burkhard König

Beilstein J. Org. Chem. 2016, 12, 2358–2363, doi:10.3762/bjoc.12.229

• (m, 4H, CH), 7.30 (m, 2H, CH); EIMS m/z: 180.0579 [M]+. Benzophenone (3b) 3b from 3a: Diphenylmethanol (73.3 mg, 0.40 mmol) and RFTA (10.9 mg, 0.020 mmol) were weighed and 74.0 mg of the mixture was used for reaction. Yield: 50%. 1H NMR (300 MHz, CDCl3) 7.83–7.79 (m, 2H, CH), 7.62–7.57 (m, 2H, CH

Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes

• H. Surya Prakash Rao and
• A. Veera Bhadra Rao

Beilstein J. Org. Chem. 2016, 12, 496–504, doi:10.3762/bjoc.12.49

• ligands as it is less expensive and more readily facilitates purification. Results and Discussion We selected the copper-mediated cross-coupling reaction of diphenylmethanol (9a) with phenylboronic acid (10a) for the synthesis of triphenylmethane (11a) to optimize the reaction conditions and catalyst

• responsible for the transformation. Thus, the optimal conditions for the copper-mediated coupling involve heating equimolar amounts of diphenylmethanol (9a) and phenylboronic acid (10a) in chlorobenzene at 80 °C in the presence of 20 mol % of Cu(OTf)2 under a blanket of oxygen-free nitrogen. Based on the

• above observations, we propose a mechanism for the copper-mediated coupling of phenylboronic acid with diphenylmethanol, leading to triphenylmethane and boric acid (Scheme 3). At the start of the cascade, the first step is the transmetallation of the copper(II) into phenylboronic acid to form reactive

Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors

• Morgan Hans,
• Jan Lorkowski,
• Albert Demonceau and
• Lionel Delaude

Beilstein J. Org. Chem. 2015, 11, 2318–2325, doi:10.3762/bjoc.11.252

• (diphenylmethyl)-4-methylphenyl)imidazolium chloride (IDip*·HCl). The synthesis of this stable precursor was accomplished in three steps starting from commercially available reagents (Scheme 9). First, p-toluidine was dialkylated with diphenylmethanol (benzhydrol) in the presence of stoichiometric amounts of HCl